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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m301.
Published online 2010 February 13. doi:  10.1107/S1600536810005155
PMCID: PMC2983743

N-(Ferrocenylmethyl)­dodecan-1-amine

Abstract

The title compound, [Fe(C5H5)(C18H32N)], was synthesized by the amination of ferrocenecarbaldehyde. In the complex, the two cyclo­penta­dienyl (Cp) rings are almost parallel with a dihedral angle of 1.36 (8)°, and are separated by a centroid–centroid distance of 3.299 (2) Å. In the crystal, adjacent mol­ecules are linked into a one-dimensional supra­molecular structure via weak C—H(...)π inter­actions between the Cp ring H atom and the Cp ring.

Related literature

For the applications of ferrocene in drug design, see: Atteke et al. (2003 [triangle]); Baramee et al. (2006 [triangle]). For linear ferrocene compounds in supra­molecular chemisty, see: Zhang et al. (2010 [triangle]). For a related structure, see: Zheng & Liu (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m301-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C18H32N)]
  • M r = 383.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m301-efi1.jpg
  • a = 26.7005 (6) Å
  • b = 8.0549 (2) Å
  • c = 10.0069 (2) Å
  • β = 97.534 (1)°
  • V = 2133.60 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.71 mm−1
  • T = 293 K
  • 0.30 × 0.26 × 0.18 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.815, T max = 0.881
  • 20623 measured reflections
  • 4900 independent reflections
  • 3892 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.112
  • S = 1.09
  • 4900 reflections
  • 228 parameters
  • H-atom parameters constrained
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT-Plus (Bruker, 2007 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005155/hy2280sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005155/hy2280Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The high lipophilicity and electrochemical behaviour of ferrocene render it very attractive for drug design. The incorporation of a ferrocenyl moiety into the 'standard' drug offers new possibilities in therapeutic applications and reversal of drug resistances (Atteke et al., 2003; Baramee et al., 2006). On the other hand, the linear compounds derived from ferrocene have shown great useful functions in supramolecular chemisty (Zhang et al., 2010). In this paper, we report the synthesis and crystal structure of the title compound.

As shown in Fig. 1, the title compound has a tadpole-typed molecular configuration. The planes of two cyclopentadienyl (Cp) rings in the ferrocene scaffold are approximately parallel with a centroid–centroid distance of 3.299 (2) Å and a dihedral angle of 1.36 (8)°. The Fe—C bond distances are in the range of 2.0295 (18) to 2.0502 (16) Å (Table 1), which are consistent with those data in the similar compounds previously reported (Zheng & Liu, 2009). The adjacent molecules are linked by weak C—H···π interactions between ferrocene cores (Table 2), forming a one-dimensional supramolecular architecture as shown in Fig. 2.

Experimental

A mixture of ferrocenecarbaldehyde (2.415 g, 0.01 mol) and lauryl amine (0.08 mol) in anhydrous methanol (50 ml) was stirred and kept refluxing for 12 h under a nitrogen atmosphere in dark place. NaBH4 (0.110 g, 2.9 mmol) was added in small portions. The mixture was stirred for 15 h, and 10 ml acetone was added to stop the reaction. The mixture was extracted with CH2Cl2 (30 ml) 10 min later. The combined organic phase was dried with anhydrous Na2SO4, and then evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, petroleum ether : ethyl acetate = 5:1 by volume) to give the title compound as yellow powder (yield 1.545 g, 80.7%). Single crystals were grown in a mixed solution of hexane/ethyl acetate (2:1 by volume) at room temperature.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.98 (CH), 0.97 (CH2) and 0.96 (CH3) Å and N—H = 0.86 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A packing diagram of the title compound along the b axis.

Crystal data

[Fe(C5H5)(C18H32N)]F(000) = 832
Mr = 383.39Dx = 1.194 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8358 reflections
a = 26.7005 (6) Åθ = 2.3–27.4°
b = 8.0549 (2) ŵ = 0.71 mm1
c = 10.0069 (2) ÅT = 293 K
β = 97.534 (1)°Prism, orange
V = 2133.60 (8) Å30.30 × 0.26 × 0.18 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer4900 independent reflections
Radiation source: fine-focus sealed tube3892 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] and ω scansθmax = 27.5°, θmin = 0.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −34→34
Tmin = 0.815, Tmax = 0.881k = −10→9
20623 measured reflectionsl = −12→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.112w = 1/[σ2(Fo2) + (0.0649P)2 + 0.2305P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
4900 reflectionsΔρmax = 0.44 e Å3
228 parametersΔρmin = −0.37 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0051 (7)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C1−0.25735 (8)0.8925 (3)0.3331 (2)0.0855 (7)
H1A−0.24950.99310.28870.128*
H1B−0.29240.89260.34530.128*
H1C−0.25050.79880.27910.128*
C2−0.22527 (7)0.8816 (3)0.4689 (2)0.0688 (6)
H2A−0.23420.97240.52480.083*
H2B−0.23310.77870.51210.083*
C3−0.16928 (7)0.8879 (3)0.46240 (19)0.0569 (4)
H3A−0.16160.98960.41740.068*
H3B−0.16030.79580.40780.068*
C4−0.13669 (6)0.8803 (3)0.59851 (18)0.0570 (5)
H4A−0.14520.97370.65250.068*
H4B−0.14480.77960.64430.068*
C5−0.08054 (6)0.8833 (3)0.59124 (19)0.0558 (4)
H5A−0.07260.98230.54290.067*
H5B−0.07190.78790.53970.067*
C6−0.04805 (6)0.8813 (3)0.72736 (18)0.0558 (4)
H6A−0.05640.97760.77830.067*
H6B−0.05640.78320.77620.067*
C70.00828 (6)0.8818 (3)0.72004 (18)0.0557 (4)
H7A0.01650.97850.66950.067*
H7B0.01670.78420.67080.067*
C80.04069 (6)0.8834 (3)0.85633 (19)0.0555 (4)
H8A0.03190.78790.90770.067*
H8B0.03280.98230.90480.067*
C90.09721 (6)0.8801 (3)0.84908 (18)0.0555 (4)
H9A0.10520.78020.80200.067*
H9B0.10590.97440.79640.067*
C100.12966 (6)0.8847 (3)0.98511 (18)0.0546 (4)
H10A0.12020.79271.03910.066*
H10B0.12270.98661.03080.066*
C110.18590 (6)0.8749 (3)0.97731 (18)0.0558 (4)
H11A0.19300.77170.93350.067*
H11B0.19530.96530.92160.067*
C120.21815 (6)0.8834 (3)1.11265 (18)0.0558 (4)
H12A0.21320.99011.15400.067*
H12B0.20760.79761.17090.067*
C130.30453 (6)0.8840 (3)1.22683 (17)0.0544 (4)
H13A0.29530.80501.29250.065*
H13B0.29980.99481.26110.065*
C140.35911 (6)0.8607 (2)1.21065 (17)0.0483 (4)
C150.37909 (7)0.7502 (2)1.12038 (19)0.0560 (4)
H150.35940.67871.05370.067*
C160.43262 (8)0.7632 (3)1.1426 (2)0.0698 (6)
H160.45630.70161.09430.084*
C170.44560 (7)0.8800 (3)1.2456 (2)0.0731 (6)
H170.48000.91371.28170.088*
C180.40041 (7)0.9412 (3)1.28863 (18)0.0591 (5)
H180.39811.02411.35930.071*
C190.39885 (9)1.2394 (3)1.0622 (2)0.0687 (6)
H190.39711.32321.13250.082*
C200.35736 (7)1.1625 (2)0.98373 (19)0.0597 (5)
H200.32161.18310.98990.072*
C210.37662 (8)1.0532 (3)0.89473 (19)0.0596 (5)
H210.35660.98290.82790.071*
C220.42930 (8)1.0612 (3)0.9174 (2)0.0639 (5)
H220.45250.99710.86930.077*
C230.44322 (7)1.1742 (3)1.0199 (2)0.0680 (6)
H230.47791.20431.05630.082*
Fe10.401688 (8)0.98868 (3)1.08888 (2)0.04257 (11)
N10.27153 (5)0.8617 (2)1.10053 (15)0.0577 (4)
H10.28250.83791.02580.069*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0610 (13)0.1023 (19)0.0867 (16)−0.0100 (12)−0.0147 (12)0.0247 (14)
C20.0478 (10)0.0909 (16)0.0660 (12)−0.0064 (10)0.0012 (9)0.0139 (11)
C30.0481 (10)0.0660 (11)0.0557 (11)−0.0037 (8)0.0038 (8)0.0017 (9)
C40.0462 (9)0.0722 (12)0.0524 (10)−0.0024 (8)0.0063 (8)0.0028 (9)
C50.0452 (9)0.0680 (12)0.0538 (10)−0.0006 (8)0.0057 (8)−0.0001 (9)
C60.0442 (9)0.0686 (12)0.0546 (10)−0.0006 (8)0.0069 (8)0.0008 (9)
C70.0444 (9)0.0677 (12)0.0549 (10)−0.0004 (8)0.0063 (8)−0.0007 (9)
C80.0439 (9)0.0677 (12)0.0552 (10)−0.0006 (8)0.0081 (8)−0.0008 (9)
C90.0444 (9)0.0674 (12)0.0553 (11)−0.0009 (8)0.0090 (8)−0.0011 (9)
C100.0421 (9)0.0679 (12)0.0541 (10)0.0003 (8)0.0076 (8)−0.0011 (9)
C110.0430 (9)0.0709 (12)0.0542 (10)−0.0015 (8)0.0085 (8)0.0015 (9)
C120.0408 (9)0.0704 (12)0.0571 (11)−0.0005 (8)0.0098 (8)−0.0004 (9)
C130.0451 (9)0.0702 (12)0.0488 (10)−0.0006 (8)0.0099 (8)0.0018 (8)
C140.0450 (9)0.0577 (10)0.0422 (8)0.0011 (8)0.0057 (7)0.0087 (7)
C150.0598 (11)0.0504 (10)0.0601 (11)0.0051 (8)0.0169 (9)0.0106 (8)
C160.0587 (12)0.0736 (13)0.0800 (15)0.0258 (10)0.0200 (10)0.0332 (12)
C170.0439 (10)0.1064 (18)0.0655 (13)0.0029 (11)−0.0057 (9)0.0377 (13)
C180.0569 (11)0.0795 (12)0.0391 (9)−0.0042 (10)−0.0007 (8)0.0119 (9)
C190.1042 (18)0.0467 (10)0.0548 (11)0.0008 (10)0.0089 (11)−0.0005 (8)
C200.0475 (9)0.0644 (11)0.0671 (12)0.0135 (9)0.0077 (9)0.0209 (10)
C210.0716 (13)0.0614 (11)0.0421 (9)0.0004 (10)−0.0060 (9)0.0084 (9)
C220.0663 (12)0.0721 (12)0.0580 (12)0.0155 (11)0.0253 (10)0.0193 (10)
C230.0512 (10)0.0744 (13)0.0760 (14)−0.0130 (10)−0.0002 (10)0.0244 (11)
Fe10.03650 (15)0.05241 (17)0.03810 (16)0.00326 (9)0.00232 (10)0.00551 (9)
N10.0407 (7)0.0843 (11)0.0486 (8)−0.0016 (7)0.0081 (6)−0.0071 (8)

Geometric parameters (Å, °)

C1—C21.511 (3)C12—H12B0.9700
C1—H1A0.9600C13—N11.454 (2)
C1—H1B0.9600C13—C141.499 (2)
C1—H1C0.9600C13—H13A0.9700
C2—C31.506 (2)C13—H13B0.9700
C2—H2A0.9700C14—C151.421 (2)
C2—H2B0.9700C14—C181.421 (3)
C3—C41.518 (2)C14—Fe12.0502 (16)
C3—H3A0.9700C15—C161.421 (3)
C3—H3B0.9700C15—Fe12.0501 (18)
C4—C51.511 (2)C15—H150.9800
C4—H4A0.9700C16—C171.406 (3)
C4—H4B0.9700C16—Fe12.038 (2)
C5—C61.516 (2)C16—H160.9800
C5—H5A0.9700C17—C181.421 (3)
C5—H5B0.9700C17—Fe12.0295 (18)
C6—C71.515 (2)C17—H170.9800
C6—H6A0.9700C18—Fe12.0398 (18)
C6—H6B0.9700C18—H180.9800
C7—C81.516 (2)C19—C231.411 (3)
C7—H7A0.9700C19—C201.414 (3)
C7—H7B0.9700C19—Fe12.038 (2)
C8—C91.520 (2)C19—H190.9800
C8—H8A0.9700C20—C211.398 (3)
C8—H8B0.9700C20—Fe12.0350 (17)
C9—C101.515 (2)C20—H200.9800
C9—H9A0.9700C21—C221.397 (3)
C9—H9B0.9700C21—Fe12.0375 (18)
C10—C111.516 (2)C21—H210.9800
C10—H10A0.9700C22—C231.386 (3)
C10—H10B0.9700C22—Fe12.0398 (18)
C11—C121.508 (2)C22—H220.9800
C11—H11A0.9700C23—Fe12.0347 (19)
C11—H11B0.9700C23—H230.9800
C12—N11.457 (2)N1—H10.8600
C12—H12A0.9700
C2—C1—H1A109.5C17—C16—H16126.0
C2—C1—H1B109.5C15—C16—H16126.0
H1A—C1—H1B109.5Fe1—C16—H16126.0
C2—C1—H1C109.5C16—C17—C18108.48 (19)
H1A—C1—H1C109.5C16—C17—Fe170.11 (11)
H1B—C1—H1C109.5C18—C17—Fe169.95 (10)
C3—C2—C1114.09 (18)C16—C17—H17125.8
C3—C2—H2A108.7C18—C17—H17125.8
C1—C2—H2A108.7Fe1—C17—H17125.8
C3—C2—H2B108.7C17—C18—C14107.7 (2)
C1—C2—H2B108.7C17—C18—Fe169.17 (11)
H2A—C2—H2B107.6C14—C18—Fe170.06 (10)
C2—C3—C4114.54 (16)C17—C18—H18126.2
C2—C3—H3A108.6C14—C18—H18126.2
C4—C3—H3A108.6Fe1—C18—H18126.2
C2—C3—H3B108.6C23—C19—C20107.33 (19)
C4—C3—H3B108.6C23—C19—Fe169.62 (12)
H3A—C3—H3B107.6C20—C19—Fe169.58 (11)
C5—C4—C3114.32 (15)C23—C19—H19126.3
C5—C4—H4A108.7C20—C19—H19126.3
C3—C4—H4A108.7Fe1—C19—H19126.3
C5—C4—H4B108.7C21—C20—C19107.65 (17)
C3—C4—H4B108.7C21—C20—Fe170.03 (10)
H4A—C4—H4B107.6C19—C20—Fe169.78 (11)
C4—C5—C6114.27 (15)C21—C20—H20126.2
C4—C5—H5A108.7C19—C20—H20126.2
C6—C5—H5A108.7Fe1—C20—H20126.2
C4—C5—H5B108.7C22—C21—C20108.31 (19)
C6—C5—H5B108.7C22—C21—Fe170.06 (11)
H5A—C5—H5B107.6C20—C21—Fe169.83 (10)
C7—C6—C5114.28 (15)C22—C21—H21125.8
C7—C6—H6A108.7C20—C21—H21125.8
C5—C6—H6A108.7Fe1—C21—H21125.8
C7—C6—H6B108.7C23—C22—C21108.50 (19)
C5—C6—H6B108.7C23—C22—Fe169.92 (11)
H6A—C6—H6B107.6C21—C22—Fe169.88 (11)
C6—C7—C8114.18 (15)C23—C22—H22125.7
C6—C7—H7A108.7C21—C22—H22125.7
C8—C7—H7A108.7Fe1—C22—H22125.7
C6—C7—H7B108.7C22—C23—C19108.21 (19)
C8—C7—H7B108.7C22—C23—Fe170.32 (11)
H7A—C7—H7B107.6C19—C23—Fe169.84 (11)
C7—C8—C9114.20 (15)C22—C23—H23125.9
C7—C8—H8A108.7C19—C23—H23125.9
C9—C8—H8A108.7Fe1—C23—H23125.9
C7—C8—H8B108.7C17—Fe1—C23107.07 (9)
C9—C8—H8B108.7C17—Fe1—C20159.10 (10)
H8A—C8—H8B107.6C23—Fe1—C2067.99 (8)
C10—C9—C8114.26 (15)C17—Fe1—C21158.62 (10)
C10—C9—H9A108.7C23—Fe1—C2167.35 (9)
C8—C9—H9A108.7C20—Fe1—C2140.14 (8)
C10—C9—H9B108.7C17—Fe1—C19122.45 (10)
C8—C9—H9B108.7C23—Fe1—C1940.54 (8)
H9A—C9—H9B107.6C20—Fe1—C1940.63 (8)
C9—C10—C11113.96 (15)C21—Fe1—C1967.69 (9)
C9—C10—H10A108.8C17—Fe1—C1640.44 (9)
C11—C10—H10A108.8C23—Fe1—C16121.59 (8)
C9—C10—H10B108.8C20—Fe1—C16159.64 (10)
C11—C10—H10B108.8C21—Fe1—C16123.34 (10)
H10A—C10—H10B107.7C19—Fe1—C16157.65 (9)
C12—C11—C10113.83 (15)C17—Fe1—C1840.89 (8)
C12—C11—H11A108.8C23—Fe1—C18123.36 (9)
C10—C11—H11A108.8C20—Fe1—C18123.53 (8)
C12—C11—H11B108.8C21—Fe1—C18159.49 (9)
C10—C11—H11B108.8C19—Fe1—C18108.01 (9)
H11A—C11—H11B107.7C16—Fe1—C1868.47 (9)
N1—C12—C11111.68 (14)C17—Fe1—C22122.53 (8)
N1—C12—H12A109.3C23—Fe1—C2239.76 (9)
C11—C12—H12A109.3C20—Fe1—C2267.54 (8)
N1—C12—H12B109.3C21—Fe1—C2240.06 (8)
C11—C12—H12B109.3C19—Fe1—C2267.50 (9)
H12A—C12—H12B107.9C16—Fe1—C22107.34 (9)
N1—C13—C14112.18 (14)C18—Fe1—C22158.80 (9)
N1—C13—H13A109.2C17—Fe1—C1568.22 (9)
C14—C13—H13A109.2C23—Fe1—C15157.63 (9)
N1—C13—H13B109.2C20—Fe1—C15124.14 (8)
C14—C13—H13B109.2C21—Fe1—C15108.60 (9)
H13A—C13—H13B107.9C19—Fe1—C15160.45 (9)
C15—C14—C18107.81 (16)C16—Fe1—C1540.68 (8)
C15—C14—C13126.77 (17)C18—Fe1—C1568.33 (9)
C18—C14—C13125.36 (17)C22—Fe1—C15122.93 (9)
C15—C14—Fe169.72 (10)C17—Fe1—C1468.47 (7)
C18—C14—Fe169.27 (10)C23—Fe1—C14160.09 (9)
C13—C14—Fe1128.60 (12)C20—Fe1—C14108.84 (7)
C14—C15—C16107.96 (18)C21—Fe1—C14123.81 (8)
C14—C15—Fe169.72 (10)C19—Fe1—C14124.22 (8)
C16—C15—Fe169.20 (11)C16—Fe1—C1468.43 (7)
C14—C15—H15126.0C18—Fe1—C1440.67 (7)
C16—C15—H15126.0C22—Fe1—C14159.01 (9)
Fe1—C15—H15126.0C15—Fe1—C1440.56 (7)
C17—C16—C15108.06 (18)C13—N1—C12113.63 (14)
C17—C16—Fe169.45 (12)C13—N1—H1123.2
C15—C16—Fe170.12 (10)C12—N1—H1123.2
C1—C2—C3—C4178.87 (19)C22—C21—Fe1—C14−161.73 (13)
C2—C3—C4—C5178.88 (17)C20—C21—Fe1—C1478.98 (14)
C3—C4—C5—C6178.17 (17)C23—C19—Fe1—C1777.97 (15)
C4—C5—C6—C7179.15 (16)C20—C19—Fe1—C17−163.53 (12)
C5—C6—C7—C8178.77 (16)C20—C19—Fe1—C23118.50 (18)
C6—C7—C8—C9178.73 (16)C23—C19—Fe1—C20−118.50 (18)
C7—C8—C9—C10179.00 (16)C23—C19—Fe1—C21−80.76 (14)
C8—C9—C10—C11177.84 (16)C20—C19—Fe1—C2137.75 (12)
C9—C10—C11—C12178.69 (16)C23—C19—Fe1—C1643.6 (3)
C10—C11—C12—N1175.96 (16)C20—C19—Fe1—C16162.1 (2)
N1—C13—C14—C15−33.2 (2)C23—C19—Fe1—C18120.63 (13)
N1—C13—C14—C18149.91 (17)C20—C19—Fe1—C18−120.86 (12)
N1—C13—C14—Fe159.3 (2)C23—C19—Fe1—C22−37.26 (12)
C18—C14—C15—C16−0.18 (19)C20—C19—Fe1—C2281.24 (13)
C13—C14—C15—C16−177.53 (16)C23—C19—Fe1—C15−163.6 (2)
Fe1—C14—C15—C1658.82 (12)C20—C19—Fe1—C15−45.1 (3)
C18—C14—C15—Fe1−59.00 (12)C23—C19—Fe1—C14162.61 (12)
C13—C14—C15—Fe1123.65 (17)C20—C19—Fe1—C14−78.89 (13)
C14—C15—C16—C170.2 (2)C15—C16—Fe1—C17119.18 (16)
Fe1—C15—C16—C1759.31 (14)C17—C16—Fe1—C2379.02 (14)
C14—C15—C16—Fe1−59.14 (12)C15—C16—Fe1—C23−161.80 (12)
C15—C16—C17—C18−0.1 (2)C17—C16—Fe1—C20−167.86 (19)
Fe1—C16—C17—C1859.64 (14)C15—C16—Fe1—C20−48.7 (3)
C15—C16—C17—Fe1−59.72 (12)C17—C16—Fe1—C21161.17 (12)
C16—C17—C18—C140.0 (2)C15—C16—Fe1—C21−79.65 (14)
Fe1—C17—C18—C1459.71 (13)C17—C16—Fe1—C1947.3 (3)
C16—C17—C18—Fe1−59.74 (14)C15—C16—Fe1—C19166.45 (19)
C15—C14—C18—C170.1 (2)C17—C16—Fe1—C18−37.81 (12)
C13—C14—C18—C17177.53 (16)C15—C16—Fe1—C1881.37 (12)
Fe1—C14—C18—C17−59.15 (13)C17—C16—Fe1—C22120.13 (13)
C15—C14—C18—Fe159.28 (12)C15—C16—Fe1—C22−120.69 (12)
C13—C14—C18—Fe1−123.32 (17)C17—C16—Fe1—C15−119.18 (17)
C23—C19—C20—C21−0.4 (2)C17—C16—Fe1—C14−81.69 (12)
Fe1—C19—C20—C21−60.05 (13)C15—C16—Fe1—C1437.49 (11)
C23—C19—C20—Fe159.65 (14)C14—C18—Fe1—C17−118.95 (19)
C19—C20—C21—C220.2 (2)C17—C18—Fe1—C23−77.08 (17)
Fe1—C20—C21—C22−59.72 (13)C14—C18—Fe1—C23163.97 (11)
C19—C20—C21—Fe159.90 (13)C17—C18—Fe1—C20−161.22 (14)
C20—C21—C22—C230.1 (2)C14—C18—Fe1—C2079.83 (14)
Fe1—C21—C22—C23−59.46 (14)C17—C18—Fe1—C21166.6 (2)
C20—C21—C22—Fe159.58 (13)C14—C18—Fe1—C2147.6 (3)
C21—C22—C23—C19−0.4 (2)C17—C18—Fe1—C19−119.11 (15)
Fe1—C22—C23—C19−59.81 (14)C14—C18—Fe1—C19121.94 (13)
C21—C22—C23—Fe159.43 (14)C17—C18—Fe1—C1637.41 (14)
C20—C19—C23—C220.5 (2)C14—C18—Fe1—C16−81.54 (13)
Fe1—C19—C23—C2260.10 (14)C17—C18—Fe1—C22−45.1 (3)
C20—C19—C23—Fe1−59.62 (14)C14—C18—Fe1—C22−164.0 (2)
C16—C17—Fe1—C23−118.99 (13)C17—C18—Fe1—C1581.32 (15)
C18—C17—Fe1—C23121.61 (14)C14—C18—Fe1—C15−37.63 (11)
C16—C17—Fe1—C20168.17 (19)C17—C18—Fe1—C14118.95 (19)
C18—C17—Fe1—C2048.8 (3)C23—C22—Fe1—C17−77.16 (16)
C16—C17—Fe1—C21−47.7 (3)C21—C22—Fe1—C17163.26 (14)
C18—C17—Fe1—C21−167.1 (2)C21—C22—Fe1—C23−119.59 (18)
C16—C17—Fe1—C19−160.67 (12)C23—C22—Fe1—C2082.12 (13)
C18—C17—Fe1—C1979.94 (15)C21—C22—Fe1—C20−37.47 (13)
C18—C17—Fe1—C16−119.40 (19)C23—C22—Fe1—C21119.59 (18)
C16—C17—Fe1—C18119.40 (19)C23—C22—Fe1—C1937.97 (12)
C16—C17—Fe1—C22−78.27 (15)C21—C22—Fe1—C19−81.62 (14)
C18—C17—Fe1—C22162.33 (14)C23—C22—Fe1—C16−118.87 (14)
C16—C17—Fe1—C1537.80 (12)C21—C22—Fe1—C16121.55 (14)
C18—C17—Fe1—C15−81.60 (14)C23—C22—Fe1—C18−43.8 (3)
C16—C17—Fe1—C1481.59 (12)C21—C22—Fe1—C18−163.4 (2)
C18—C17—Fe1—C14−37.81 (13)C23—C22—Fe1—C15−160.77 (12)
C22—C23—Fe1—C17120.69 (14)C21—C22—Fe1—C1579.64 (14)
C19—C23—Fe1—C17−120.31 (14)C23—C22—Fe1—C14166.26 (18)
C22—C23—Fe1—C20−80.88 (13)C21—C22—Fe1—C1446.7 (3)
C19—C23—Fe1—C2038.12 (12)C14—C15—Fe1—C1781.90 (12)
C22—C23—Fe1—C21−37.33 (12)C16—C15—Fe1—C17−37.58 (12)
C19—C23—Fe1—C2181.67 (13)C14—C15—Fe1—C23163.83 (18)
C22—C23—Fe1—C19−119.00 (18)C16—C15—Fe1—C2344.4 (3)
C22—C23—Fe1—C1678.93 (15)C14—C15—Fe1—C20−78.92 (13)
C19—C23—Fe1—C16−162.07 (13)C16—C15—Fe1—C20161.60 (13)
C22—C23—Fe1—C18162.56 (12)C14—C15—Fe1—C21−120.65 (12)
C19—C23—Fe1—C18−78.44 (15)C16—C15—Fe1—C21119.88 (13)
C19—C23—Fe1—C22119.00 (18)C14—C15—Fe1—C19−45.1 (3)
C22—C23—Fe1—C1546.6 (3)C16—C15—Fe1—C19−164.6 (2)
C19—C23—Fe1—C15165.58 (19)C14—C15—Fe1—C16119.48 (16)
C22—C23—Fe1—C14−165.54 (18)C14—C15—Fe1—C1837.73 (11)
C19—C23—Fe1—C14−46.5 (3)C16—C15—Fe1—C18−81.75 (13)
C21—C20—Fe1—C17160.6 (2)C14—C15—Fe1—C22−162.56 (11)
C19—C20—Fe1—C1742.1 (3)C16—C15—Fe1—C2277.96 (14)
C21—C20—Fe1—C2380.51 (14)C16—C15—Fe1—C14−119.48 (16)
C19—C20—Fe1—C23−38.03 (13)C15—C14—Fe1—C17−81.23 (13)
C19—C20—Fe1—C21−118.53 (17)C18—C14—Fe1—C1738.01 (14)
C21—C20—Fe1—C19118.53 (17)C13—C14—Fe1—C17157.32 (19)
C21—C20—Fe1—C16−41.8 (3)C15—C14—Fe1—C23−161.9 (2)
C19—C20—Fe1—C16−160.4 (2)C18—C14—Fe1—C23−42.6 (3)
C21—C20—Fe1—C18−163.16 (13)C13—C14—Fe1—C2376.7 (3)
C19—C20—Fe1—C1878.31 (14)C15—C14—Fe1—C20120.88 (12)
C21—C20—Fe1—C2237.40 (13)C18—C14—Fe1—C20−119.89 (13)
C19—C20—Fe1—C22−81.13 (14)C13—C14—Fe1—C20−0.57 (18)
C21—C20—Fe1—C15−78.09 (14)C15—C14—Fe1—C2178.92 (13)
C19—C20—Fe1—C15163.37 (11)C18—C14—Fe1—C21−161.85 (13)
C21—C20—Fe1—C14−120.49 (12)C13—C14—Fe1—C21−42.53 (19)
C19—C20—Fe1—C14120.98 (12)C15—C14—Fe1—C19163.35 (12)
C22—C21—Fe1—C17−41.8 (3)C18—C14—Fe1—C19−77.42 (14)
C20—C21—Fe1—C17−161.1 (2)C13—C14—Fe1—C1941.90 (19)
C22—C21—Fe1—C2337.06 (13)C15—C14—Fe1—C16−37.61 (12)
C20—C21—Fe1—C23−82.23 (13)C18—C14—Fe1—C1681.63 (14)
C22—C21—Fe1—C20119.30 (18)C13—C14—Fe1—C16−159.05 (19)
C22—C21—Fe1—C1981.10 (14)C15—C14—Fe1—C18−119.24 (16)
C20—C21—Fe1—C19−38.20 (12)C13—C14—Fe1—C18119.3 (2)
C22—C21—Fe1—C16−76.83 (16)C15—C14—Fe1—C2244.6 (2)
C20—C21—Fe1—C16163.88 (12)C18—C14—Fe1—C22163.9 (2)
C22—C21—Fe1—C18162.9 (2)C13—C14—Fe1—C22−76.8 (3)
C20—C21—Fe1—C1843.6 (3)C18—C14—Fe1—C15119.24 (16)
C20—C21—Fe1—C22−119.30 (18)C13—C14—Fe1—C15−121.4 (2)
C22—C21—Fe1—C15−119.41 (13)C14—C13—N1—C12179.95 (15)
C20—C21—Fe1—C15121.30 (12)C11—C12—N1—C13174.70 (16)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C19–C23 ring.
D—H···AD—HH···AD···AD—H···A
C18—H18···Cg1i0.982.963.870 (2)155

Symmetry codes: (i) x, −y+5/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2280).

References

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